February 11, 2019

The Secret Early Lives of Sam Esmail

by Without Fail

Director and screenwriter Sam Esmail's TV series Mr. Robot was an immediate hit when it premiered in 2015, turning him into one of the most in-demand showrunners in Hollywood. But he didn't have an easy path to that point. Sam was 38 by the time Mr. Robot launched. He'd worked all kinds of jobs — including a stint as a startup founder — and seen all kinds of setbacks. Sam tells Alex about the stuff that came before, and about why he couldn't quit trying to make movies, even when success was a long way off.

Without Fail is hosted by Alex Blumberg. It is produced by Molly Messick and Sarah Platt and edited by Alex Blumberg and Devon Taylor. 


Peter Leonard mixed the episode. Theme and ad music by Bobby Lord.


Transcript

ALEX: From Gimlet Media, I’m Alex Blumberg and this is Without Fail, the show where I talk with entrepreneurs, artists, athletes, visionaries of all kinds about their successes, and their failures, and what they’ve learned from both. 


We are back! Last year, we did a pilot season of this show. To see whether people would like it. Whether they wanted us to keep going. And they did! So now, we’re back.  We’ll have new episodes three times a month… from now ‘til forever. Ask and you will receive… so if you haven’t subscribed yet… go ahead sign up.


And on our first show back today, I’m talking with one of the hottest directors and showrunners in Hollywood. Sam Esmail, the person behind the hit show Mr. Robot. And most recently, the hit series on Amazon. Homecoming. Starring Julia Roberts. Homecoming was also critically acclaimed, and nominated for 3 Golden Globe awards. Although it didn’t win any of them.


Now, people familiar with me, or Gimlet, the company I co-founded, which makes this podcast you’re listening to now, and many others, might remember ... Homecoming, began its life as a Gimlet podcast. We were very involved in the making of that show, and in fact, I did a whole series of stories on turning the podcast into a TV show. And the reason I was very excited to talk to Sam Esmail on Without Fail, came out of an interview I did for that series. 


I was interviewing Sam Esmail, along with Julia Roberts, and there was a moment from that conversation that stuck with me. It’s a moment when Julia was raving about Sam.


JULIA: I mean I think Sam is incredibly good at understanding people and how we work and what makes people, um, as highly creative as they can be and -- and as highly motivated as they can be.

ALEX: To hear you both talk it really does sound like you both… it was really this sort of like almost instant creative coming together in a weird way. Has that happened before or was that unusual?

SAM: Oh it’s -- I mean, I’ve done one movie and I’ve done one television show outside of this, so my experience is limited. But the fact that she and I hit it off so quickly so early is practically unheard of. //

SAM: I mean the first thing we do is, like -- 

JULIA: we yell

SAM: we yell each other’s names. 

JULIA: Hug.

SAM: And then we hug.

JULIA: It’s true. Every day.

SAM: Yeah.


Listening to them talk I was struck by how crazy all this must have been for Sam. Like, before Mr. Robot came out, just three years earlier, no one had ever heard of Sam Esmail. And now, here he was palling around with Julia Roberts, one of the biggest movie stars in history, with a career spanning more than a quarter of a century, like it was nothing. Sam, he’s old, in Hollywood years. Over 40. He’d been trying to make it as a filmmaker for decades, the very same decades that Julia Roberts had been winning Oscars, and setting box office records and becoming the highest paid actress in Hollywood history. What was it like to struggle that long, and then have his breakthrough be so sudden, meteoric, and happen so relatively late. 


And so that is what I wanted to talk to him about. And so I invited him back to our studios for a conversation.


ALEX: You -- you've had a lot of success now, but it was a long time coming.

SAM: Yes. Did not have a lot of success prior to that, yeah. 

ALEX: So I want to talk about the prior. 

SAM: Yes.


And so we did. And it turns out that the prior … the long winding path through multiple failures that led Sam to where he is now, is an incredibly fascinating story that goes places I never expected. A story that starts a long time back. In his childhood. With his early love of movies. And not necessarily kid movies. 


SAM: I remember very early on watching -- this is going to sound so pretentious, but it's true. It's -- I was watching French Connection. I must have been like five or something or maybe even younger? Four?

ALEX: Four or five, watching the French Connection? 

SAM ESMAIL: French -- The French Connection. And I just remember that car chase scene. You know, where it -- where it's -- they're about to hit the baby carriage, and you're just like freaking out. And then the baby carriage has no baby. It's just a bunch of garbage in there. And I just -- that moment specifically stuck out to me. And -- and I remember watching that movie pretty obsessively. But it wasn't until I saw E.T. that -- that's when I started to think about doing it myself.

ALEX: So how old were you at this point? 

SAM ESMAIL: So now I think I'm about eight.

ALEX BLUMBERG: Uh-huh.

SAM ESMAIL: Or maybe seven. And -- and it's the first movie I saw in the theater. My parents were really -- they didn't understand, they had no kind of way to contextualize why I was so obsessed with movies, because they weren't -- they weren't -- a) they weren't American, and b) they -- they grew up in Egypt and they didn't really have movie theaters. 

ALEX BLUMBERG: Okay.

SAM ESMAIL: So ... 

ALEX BLUMBERG: So this was a completely American phenomenon to them, going to the movies? 

SAM: Yes.

[CROSSTALK]

SAM ESMAIL: And they didn't -- and the popcorn and, like, they just thought the whole thing was ridiculous. 

ALEX BLUMBERG: The popcorn is ridiculous, by the way.

SAM ESMAIL: It is.

ALEX BLUMBERG: It's so expensive.

SAM ESMAIL: I mean, they're not wrong. They're not wrong. But worth it. But -- they actually didn't go into the movies with me, because they didn't want to buy a ticket for themselves. They would -- buy a ticket just for me, and send me in by myself and then just pick me up later. They did that actually throughout my -- they never went to the movies with me. They would only just drop me off. But um when I was seven and they dropped me off to see E.T. -- the reason why I wanted to go was -- I mean, everybody in school was talking about it. Oh my god, E.T., it was the biggest thing. And, because I was kind of quietly growing this obsession at home with movies, I thought, "Oh my god, this is just going to blow my mind." And I go in and I watch it, and I am bored beyond belief.

ALEX BLUMBERG: Really? 

SAM ESMAIL: Yeah. I mean, it was just sort of this domestic drama about this relationship between this kid and the alien. And I'm like, "Where are the chase sequences? Where is the action? Where's the fun?" And I just didn't have any fun at all. I didn't care about the Reese's Pieces, and the dressing E.T. up as a girl, and the frogs in the school. I just didn't care. I didn't care. And I walked out, and I remember thinking, "I can do better than that." And that's -- that was really, I mean, I'm -- that's when...

ALEX BLUMBERG: Suck it, Spielberg.

SAM ESMAIL: I know. By the way Spielberg, you're amazing. I really don't mean to dis on you if you happen to be listening to this. 

ALEX BLUMBERG: Call me.

SAM ESMAIL: Actually, in a weird way you inspired me to be a filmmaker, so ...

ALEX BLUMBERG: With your hack, boring movie.

SAM ESMAIL: But yeah, I just remember having that feeling like I could touch that. Like, I knew that I had specifics on what I liked, what I wanted to experience going to the movies. I kind of knew that I had a voice there. But my parents you know, they didn't want me to be a filmmaker. In fact, I remember when I was in the sixth grade, and -- and they had -- because, you know, I was -- it was very well-known in my home that I wanted to be a filmmaker. I used to literally take figurines like, you know, um, G.I. Joe toys or Star Wars toys, and create movies, write movies on a script and use them and time it out to the 90-minute runtime or the two-hour runtime. So they -- they saw my obsession with this, and they were worried that this was going to stick. And I remember in sixth grade at the parent-teacher conference they talked to my teacher and they said, "You know, he wants to be a filmmaker. Can you -- can you talk to him? Can you convince him not to do this?" You know? 

ALEX BLUMBERG: Right. 

SAM ESMAIL: And I remember my teacher looking at me and she asked me, “Is this true? Do you want to make movies?" And -- and I said -- and I said, "Yeah, that -- that's what I want." And she kind of looked at me and then slowly looked back, and said to my parents, "He'll grow out of it." And when she said that, I remember getting so angry that I said to myself -- I didn't say this out loud, but I said it to myself -- now, just because of what you just said, I will be a filmmaker. Like, I will never give up. I will -- this is the one thing I will do.

ALEX BLUMBERG: Wow. 

SAM ESMAIL: Yeah. 

ALEX BLUMBERG: That's fascinating. 

SAM ESMAIL: Yeah, so this is kind of -- it was a lot of spite that got me here.

ALEX BLUMBERG: Well, I think about this because I feel like spite -- there is this element of, like, "You said I couldn't do it and I'm going to prove it to you that I could." 

SAM ESMAIL: Right.

ALEX BLUMBERG: It's really powerful.

SAM ESMAIL: Yeah, there's that line, um... What's the best revenge? Lead a good life. You know?

ALEX BLUMBERG: Yes.

SAM ESMAIL: Because you're right, it's more about proving it to them, but then, you know, behind that is probably something about proving it to yourself. And then -- and for whatever reason, it fuels me. 

ALEX BLUMBERG: So you know at this age, in sixth grade you're vowing, "I'm gonna -- I'm gonna ..."

SAM ESMAIL: Yep.

ALEX BLUMBERG: "Prove my teacher wrong."

SAM ESMAIL: Yep.


And indeed, six years later, when Sam graduated from high school, he headed off to New York University, NYU, and its renowned film school. In a nod to his parents, who still didn’t want him to be a director, he minored in computer science, but majored in film. And in 1998, he graduated. 


ALEX BLUMBERG: So this is where -- so this in the -- in what -- what -- what I would now expect to happen -- and so you go get your film degree and then you go off and start making movies. But that's not in fact what happened. 

SAM ESMAIL: No.

ALEX BLUMBERG: What did -- what did you do?

SAM ESMAIL: Well, so what happened was I graduated. My parents didn't pay for my whole tuition, so I was massively in debt. And I -- and I was a computer nerd. And so I, like, what I did was I took a job working at a little internet startup, and I was trying to figure out how to get my first feature off the ground. 

ALEX BLUMBERG: Right.

SAM: And -- and while I was working at this little internet startup, I became friendly with one of the VCs that funded the startup. And this is -- this is 1998. So this is, like, the internet has exploded onto the scene, I geeked out at every site that would come up. And I would always talk to my friends about, "We should do a startup, we should do an internet startup," because, you know, I was a little arrogant prick and thought I could be better than any -- half the sites that were coming out. Because then I was like, "Well, if I can -- if I could do that, then I can get money and then fund my films." So that was really the only reason why I was interested in doing it. 

ALEX BLUMBERG: So your plan, just to put it -- say it out loud was, "I'm going to start -- as a 20-year-old -- start a super-successful company that then I can then flip in an IPO or an acquisition that will then fund my dreams of becoming a filmmaker.

SAM ESMAIL: Yeah, I mean like, I looked at -- like, I took a page, like Paul Allen from Microsoft.

ALEX BLUMBERG: Right.

SAM ESMAIL: I don't think he stayed there for very long but, you know, became a very wealthy guy.

[CROSSTALK]

ALEX BLUMBERG: No, no. I know. It's doable, but it's also like saying like, "My plan is to get into the NBA and get a billion dollars, and then retire after two years and then become ... 

SAM ESMAIL: Yeah, that is how arrogant I was. I just thought, "I'll do this little thing to do this other, I guess, other crazier thing," you know?

ALEX BLUMBERG: So, what happened? 

SAM ESMAIL: So, at the time AOL was huge.

ALEX BLUMBERG: Right.

SAM ESMAIL: And -- and I remember thinking, "God, it's so obvious why AOL is beating everyone up, because if you remember AOL's software to log in was very easy. You put in your username and password, you logged in, it dialed, and then you got in and then you've got mail. And here's your buddy list. And it just -- everything was right there. If you remember the other ISPs like AT&T or Mindspring or EarthLink, you know, they had like these real shitty dialers. And once you get in there, then you had to launch another application for your e-mail or launch another...

ALEX BLUMBERG:  And for people who don't remember it, this is -- this is how hard it was just to get -- check your e-mail back in the day. Like, they hadn't worked anything out. 

SAM ESMAIL: Right.

(CROSSTALK)

SAM ESMAIL: AOL was just like way ahead of everyone.

ALEX BLUMBERG: Uh-huh.

SAM ESMAIL: So I just thought well why not take the software that AOL did, create a -- basically the same kind of experience, and then license that out to all the ISPs.

ALEX BLUMBERG: Right. Internet service providers.

SAM ESMAIL: So they could basically get the benefit of the AOL software, and then we would make the money off the licensing. I pitched that to the VC literally with, like, a one-page pitch doc  -- I didn't know anything. I was 20. I had no business acumen or anything like that. And he loved it, gave me $6 million. 

ALEX BLUMBERG: What?

SAM ESMAIL: Yeah, but this is again -- remember, this is like the internet boom. So I had $6 million. I was 20. 

ALEX BLUMBERG: Oh my God! What did you think?

SAM ESMAIL: Yeah, I couldn't legally drink, and -- that took over my life for two years. 

ALEX BLUMBERG: You were one of those 20-year-old, just-out-of-college Web 1.0 ...

SAM ESMAIL: Yeah. 

ALEX BLUMBERG: Entrepreneurs. 

SAM ESMAIL: Yes. 

ALEX BLUMBERG: And what did -- what did your days look like back then?

SAM ESMAIL: Well, the -- the company just took over my life. I was there from, like you know, 7:00 in the morning until 2:00 in -- 2:00 am. And even when I went home I was working, and I just had to keep thinking about what -- what features can we do, how can we streamline the software devel --? And I didn't know anything about software development, you know? So it just was this weird pressure cooker for like a couple of years, where I kind of just was thrown into this world, having no clue what to do. 

ALEX BLUMBERG: And what was your title? You were the CEO?

SAM ESMAIL: I was -- I was President and CTO, and he was the CEO, the investor was. 

ALEX BLUMBERG: How many people were working for you? 

SAM ESMAIL: At, like -- at its peak, probably about 50. 

ALEX BLUMBERG: Wow.

SAM ESMAIL: Yeah. But then -- this is how stupid I was. I did not consider broadband. And then -- I mean, it was around ...

ALEX BLUMBERG: You didn't consider broadband meaning, like most ...

SAM ESMAIL: Broadband came out, then why did you need a dialer software to dial into the internet? Nobody dialed into the internet anymore. 

ALEX BLUMBERG: Right. Because you were creating a -- a solution for people when they were still connecting over their phones. 

SAM ESMAIL: Exactly. 

ALEX BLUMBERG: When did you know that it was over? 

SAM ESMAIL: I would say -- well, I don't know if there was a -- if there was a moment, but it was a combination of the business model had shifted a little bit, you know? And then -- my parents got involved again, and really encouraged me to go back to school. 

ALEX BLUMBERG: Uh-huh.

SAM ESMAIL: And so I on a whim I applied to Dartmouth. Dartmouth’s grad school for creative writing. And I get in. And I thought to myself, "Well, you know, maybe -- maybe this is a time for me to make my exit. Maybe this is -- I'm just not cut out for this." So I had an honest conversation with the investor who, I don't -- I'm pretty sure he wasn't very happy with me for leaving.

ALEX BLUMBERG: Tell me about the conversation. What happened?

SAM ESMAIL: I went to him and I said, "Look, you know, my parents are pressuring me. So I applied to Dartmouth." And I got in. I said I'd have to leave in two months. And so it was kind of short notice for the President and CTO to be -- to be leaving. And -- and he just kind of said, "Okay." He didn't really say much. He said, "Okay." 

ALEX BLUMBERG: Why do you think he was mad?

SAM ESMAIL: Because he didn't return any of my calls or emails after that.

ALEX BLUMBERG: Oh, really? 

SAM ESMAIL: Yeah. And then the company kind of went under and failed. And I'm sure he lost a lot of money, and yeah. 

ALEX BLUMBERG: And you've never spoken to him since.

SAM ESMAIL: Not -- not out of lack of trying. 

ALEX BLUMBERG: Uh-huh.

SAM ESMAIL: I've tried to reach out to him several times. He just doesn't -- he doesn't respond. 

ALEX BLUMBERG: Oh. How does that make you feel? 

SAM ESMAIL: I feel terrib -- I mean it goes back to, you know, he gave me a lot of money. He really believed in me. And the people that were working for me really believed in me and -- and I failed them. I failed them. I didn't. I didn't do a good job. 

ALEX BLUMBERG: Yeah. Wow. I'm also just imagining it from his perspective, like he's -- like, he's like this big investor. I'm imagine -- I don't know who he is, but I'm imagining, like, sort of like an investor-type person who's, like, used to, like, sort of like, taking big bets on these founders and, like, -- and like, you're in the middle of it with him, and then all of a sudden here's, like, the main guy, the person he's put the bet on is like, "I want to take a creative writing class, and the semester starts really soon, so I've got to go."


That creative writing class, in a surprise to no one, did NOT put Sam on an immediate path to fame and fortune. There was still lots of prior for him to get through. Including one of the lowliest jobs in Hollywood… which is saying a lot. That’s coming up after the break.


BREAK 1


Welcome back to Without Fail and my conversation with Sam Esmail.


So, when Sam left his tech startup, he wasn’t rich. Of the investor’s original $6 million, almost all of it had all been spent hiring employees, paying for office space and that kind of thing. Sam hadn’t paid himself much of a salary at all. 


So when he left to pursue a creative writing degree at Dartmouth, he was essentially broke. And after Dartmouth he went for more post-graduate studies. This time at the AFI Conservatory, the American Film Institute, the famous film school in Los Angeles. And when he graduated from THERE, in 2004, he found himself in a familiar situation.


SAM ESMAIL: It was the same thing as graduating from NYU. Broke. Now even more in debt, because I still had the debt from NYU. Now I have debt from AFI.

ALEX BLUMBERG: How in debt are you? Could you -- can you tell me?

SAM ESMAIL: Yeah, yeah. It was close to $200,000.

ALEX BLUMBERG: Oh my God.

SAM ESMAIL: Yeah. And I also didn't have a job. And I also -- hate -- hated Los -- I still do not like Los Angeles. Do not like living in Los Angeles. So the first thing I did was get a job, and the job I got was being an editor in porn. And the reason why I did that was because I became really good friends with my neighbor. And my neighbor was a porn producer. So I started editing porn films because it was hard getting a gig anywhere. So I was -- I was editing porn for a long time -- for about a year or so. And then -- and then I made the very kind of like small leap from editing porn to editing reality shows, which just kind of basically the same -- same thing if you think about it. 

ALEX BLUMBERG: So how old were you at this point? 

SAM ESMAIL: So I was 27.

ALEX BLUMBERG: 27, okay. 

SAM ESMAIL: Yeah.

ALEX BLUMBERG: And -- what's your feeling at that moment? Were you feeling like, "Alright! 

SAM ESMAIL: The -- the -- the thing that kept coming up for me was, "Well this sucks, right? But what else am I going to do?" Am I going to be a lawyer? Am I going to be a whatever? Am I going to switch careers? By the way, a lot of people from AFI from my year -- I remember one of my -- one of my good pals at AFI he literally, I think maybe two or three years after graduating, became a dentist. Went to school to be a dentist and now he's a dentist. 

ALEX BLUMBERG: Mm-hmm.

SAM ESMAIL: And there is that tricky phase, that first three to five years after graduating, and where you do have debt and where you're not making money or you're struggling, where you have to sort of consider, "Am I in it? Am I going to do this? Am I going to stay committed or not, you know?"

ALEX BLUMBERG: Did you learn in this, like, prior period of, like, the porn and reality editing -- did you learn anything about the craft of filmmaking from doing that kind of work? 

SAM ESMAIL: No.

ALEX BLUMBERG: No.

SAM ESMAIL:  No. Not at all.

ALEX BLUMBERG: Would people critique your cuts ...

SAM ESMAIL: Oh, yeah.

ALEX BLUMBERG: Did you get notes?

SAM ESMAIL: Oh yeah … That was the thing. I would try and do some interesting things, and I would always get told, "Don't do that." 

ALEX BLUMBERG: Like what? Do you remember a specific ... 

SAM ESMAIL: Well, I remember specifically with porn, I would try and stay in -- in wider shots, or -- or do these kind of weird staccato jump cuts to sound editing or whatever, and they just, "Stop, stop. We're not doing that. And don't stay in the wide. Get up really close." The thing is I, you know, I don't mind watching porn. I don't understand these tight shots where you don't see anything. It's like to me, that's not a turn on. And they're like, "No. That's our base. They love that. We're doing that." So they just -- the thinking in their heads was, "We're not trying to be artful in any way in communicating anything. We are just purely fan service. We are just purely playing for the base, because we want their money." It is completely transactional. There's no -- there's no kind of frills about that. And some people are like that just in scripted television, or scripted or feature films, you know? We -- no, we do not care about doing something interesting, or it is strictly about getting money back. And it's a business to them, you know?

ALEX BLUMBERG: It's purely business. There's no art to it at all. 

SAM ESMAIL: Correct. Correct. 

ALEX BLUMBERG: And -- once you made the jump from porn to reality, did you feel -- was there like -- was there some sort of incremental sort of progress being made in your mind, or was it still, like, was it just ... 

SAM ESMAIL: No, no, no. These were graveyard shifts. So when I was in reality, I was going in at 6:00 p.m. and working until 4:00 or 5:00 in the morning. This was a grind. This wasn't anything. This was not a learning process. This was purely just to pay the rent. 


This grind continued for several years. And then Sam got what you could call, looked at in exactly the right light, his first break. Something just a little better. A small step up. This was the mid-2000s and DVD box sets were big. Sam’s job was to help edit the extra content that went into these DVD box sets. Things like interviews with directors and filmmakers about the making of classic movies. And after editing those interviews for a while, he got pretty good at it.


SAM: What ended up happening was, I became so good at my job that they ended up making me the post-production supervisor. So I had this huge promotion with a huge salary bump, like six figures. And...

ALEX BLUMBERG: So what were you -- what were you making before, and what were you making after?

SAM ESMAIL: I mean I was probably making like 60 or 70 before, and then after I was -- I was 100, 110. 

ALEX BLUMBERG: Okay. 

SAM ESMAIL: And, you know, I don't know. I was probably -- had just turned 30 or 29 or whatever. And I remember thinking, "Well this is nice." Like, I didn't have to -- I mean, I was paycheck-to-paycheck before. 

ALEX BLUMBERG: Yeah. 

SAM ESMAIL: This was like, "Oh, I can kind of relax, and I'm on salary." So -- because as an assistant editor, I was only paid hourly.

ALEX BLUMBERG: Right.

SAM ESMAIL: So when I didn't work, I didn't make money that week. But here it's like, "No, I get paid every week whether I take a few days off or not." And it was -- it was really nice. And by the way, I was working at a great company that really -- I became friendly with all the other employees. And, you know, I remember there were like 10-year anniversaries and 20-year anniversaries of employees that had been there for 10 or 20 years.

ALEX BLUMBERG: Uh-huh.

SAM ESMAIL: And that -- that impressed me and scared me at the same time, you know? And I was just like, I don't know how -- how you could do it. 

ALEX BLUMBERG: Right. 

SAM ESMAIL: And I'm slightly horrified that you can, but -- but also incredibly impressed.

ALEX BLUMBERG: And also this is better than the graveyard shift editing porn. 

SAM ESMAIL: This is better than the graveyard shift. I could, like, have a normal life. I could have a social life. And -- and it was -- it was -- you know, there was a moment that -- where I was doing this, where I said, "This isn't that hard of a job, for me anyway, and I'm making good money. And all these people here have lived their lives, there making this money and doing the job and coming into work every day.” And there -- there was that easy conversation in my head of, "You could just do this. Could just do this, right?" It would have been easy.

ALEX BLUMBERG: And I would imagine it's very seductive, especially having gone through the couple of years prior. 

SAM ESMAIL: It was such a struggle. Such a pain in the ass. And here I am making, again a decent living. And I, you know, I was pretty young to be in that position, and, you know, I had so much potential to even make even more money and get more promotions and more vacation days and whatever. I mean, that's what people, you know, you stay five years, you get four weeks...

ALEX: I’m aware...

SAM ESMAIL: Instead of two or three… And so I'm like, "Oh, my god!" And I got -- by the way, I had a healthcare. Did not have healthcare before then.

ALEX BLUMBERG: Mm-hmm.

SAM ESMAIL: I had, like, dental. I could, like, be a real person and go to a doctor. 

ALEX BLUMBERG: How -- how -- how serious was that conversation in your mind? 

SAM ESMAIL: It wasn't very serious.

ALEX BLUMBERG: Right.

ALEX BLUMBERG: It occurred to you. 

SAM ESMAIL: It occurred to me, and I saw it every day, right? 'Cause I would see everyone kind of come in and talk about their family vacations and talk about the engagements this person had, and the baby that this person had. And it was just like this community that they were develop -- and honestly, the very tight-knit community. I mean -- I was -- I liked it. It was nice.

ALEX BLUMBERG: Yeah. 

SAM ESMAIL: But it wasn't enough. And I -- and the reason why I knew that was, I'd go home at the end of the day at 6:00 pm, and I would write until 2:00 am. And again, the thought would always occur to me, I could just not do this part. Just come home at 6:00 pm like everyone else does have dinner with whoever, go out to the movies or whatever and then go to bed.

ALEX BLUMBERG: Yeah.

SAM ESMAIL: And do this again. 

ALEX BLUMBERG: Yeah.

SAM ESMAIL: But I -- just -- it just wasn't enough. So then the conversation turned into, "Well, I'm gonna do this or die -- or die trying." And I might fail. Like, that's totally within the realm of possibility here, because this is the hardest business to get into. But I'm just not going to stop trying. And so I thought to myself, "I just might end up one of those guys that goes into his, you know, 40s or 50s and is just writing on the side, doing little gigs here and there, and just never actually makes it, you know? 

ALEX BLUMBERG: Mm-hmm.

SAM ESMAIL: But that was okay. I mean, I had to -- I mean, I wasn't, like, happy about that picture, but I had to be okay with that possibility, you know?

ALEX BLUMBERG: Was there a person like that in your life that you knew?

SAM ESMAIL: Oh yeah. Oh yeah.

ALEX BLUMBERG: Who? I mean, don't name any names, but like, who are the characters in your life ... 

SAM ESMAIL: Well, there's one person I know who has a family. He's in his 60s, he has grandkids now, and he -- he wanted to be an actor. And he's still doing little community theater things. He doesn't have a job. He gets jobs here and there, but it's really his wife is really the one that, you know, makes -- makes the income for the family and just floats from job to job. 

ALEX BLUMBERG: Yeah. 

SAM ESMAIL: Still goes on auditions. Still is an extra in, you know, in movies, and gets excited when that happens. And yeah, that's his life. 

ALEX BLUMBERG: I know, it's funny because there's like this -- there's this romantic period where, like, failure is sort of like, "Oh yeah, that's just you're -- you're -- you're on the road to success." And then there's a point at which it turns, and you're just --  and it feel -- and there's like this point where you're like, "Maybe you should have given up. Maybe you should have taken the dentist route or something." 

SAM ESMAIL: I guess it just never -- that never occurred to me. I guess it just never occurred to me that I would do that, because I didn't understand what would be the point. Like, you know...

ALEX BLUMBERG: You wanted to be that guy rather than a successful dentist. Was that what you were ...?

SAM ESMAIL: I don't -- I wouldn't rather be that guy than a successful dentist, but I know being a successful dentist would always end up with me quitting and going back. Like, you know what I mean? Like, I would always -- I would always just leave, which is what I kept doing. That was my pattern, you know? I just knew it was impossible for me to just try ... 

ALEX BLUMBERG: It was that guy or bust, basically. 

SAM ESMAIL: Exactly. 


Coming up, Sam’s actual big break. Right after our commercial break. 


BREAK 2


Welcome back to Without Fail and my conversation with Mr. Robot creator and Homecoming director Sam Esmail.


So, while Sam was working at the post-production place, one of the scripts that he’d been writing in his free time, nights and weekends, attracted some buzz. It got featured on a hot website for unpublished scripts called The Blacklist. Nobody actually acquired that script, but he continued trying. He made an independent feature called Comet, which got released, but that nobody seemed to like that much. It got panned by critics, and closed in just a couple weeks. And then, finally, his actual big break came. He’d been pitching a script that he’d been working on for years, Mr. Robot. He’d taken it to most networks in town and they’d all passed. But then, USA said ‘we want to make it.’ Mr. Robot features a young, troubled hacker named Elliot, and a shadowy man who runs an international hacking ring, who goes by the moniker Mr. Robot. 


And when USA picked up the show, that is when the prior finally gave way to the present, when Sam’s life started to shift … to feel different from the one he’d been living for the past 37 years. 


He says the magnitude of the shift, it really struck him during casting for that first season of Mr. Robot. This is early in the process, they have a script, and now they’re looking for actors to play the roles. And Sam remembers being blown away by the caliber of actor that he, Sam Esmail, was getting to choose from. 


SAM ESMAIL: Normally, you know, when I was making Comet, you're just begging, you're hoping anybody that you see on TV or at the movies would be in it. You know, you are just like, there's no audition, you're just, like, hoping that they'd say yes. 

ALEX BLUMBERG: Who can I get? Because I can't even pay them. 

SAM ESMAIL: Right.

ALEX BLUMBERG: Right. Yeah.

SAM ESMAIL: Right. Here it's like, "Oh no, you guys are coming in to audition for me, and I have to pick." That was -- that was really surreal.

ALEX BLUMBERG: I never thought about that, but it is a pretty -- almost a complete flipping of the power structure that almost never happens in real life. Where all -- where like, literally you're the beggar. 

SAM ESMAIL: Yes. 

ALEX BLUMBERG: And they have all the power. 

SAM ESMAIL: Yes. 

ALEX BLUMBERG: And then it just like fully flips 180 degrees.

SAM ESMAIL: And it was crazy, especially the Mr. Robot role?

ALEX BLUMBERG: Uh-huh?

SAM ESMAIL: And because it's older, like, guys I grew up watching, including -- including the guy I ended up casting, were coming into to try out for this job, for this -- for this thing I wrote. And they're reading my dialogue. You know, that’s surreal.

[CROSSTALK]

SAM ESMAIL: I mean Christian Slater. 

ALEX BLUMBERG: He got the role, right? 

SAM ESMAIL: He got the role, yeah. 

ALEX BLUMBERG: And, like, what was that like -- because you'd seen him I'm sure, right? Like, growing up watching him?

SAM ESMAIL: Oh yeah. I mean look, Pump Up The Volume was one of those movies on the VHS tape that I repeatedly watched until it broke. 

ALEX: Yeah, that must have been so strange.

SAM ESMAIL: That's the surrealness. And then you -- and then by the time you get up on set, it's kind of like things are in -- I mean, things are, you know -- that's surreal too, because there's a huge company now of 150 people or so coming together to do this. But -- but I think then you're into the process, and it's less about the kind of overwhelming impact of it and more about now can I get this right. Because, you know, that was the other thing that was in the back of my head: what if this doesn't turn out to be good? 

ALEX BLUMBERG: Right. 

SAM ESMAIL: How many more chances do I get here, you know?

ALEX BLUMBERG: Yeah, because, like, the one thing that you had released, your indie feature Comet had, like, closed within the first month that it opened. 

SAM ESMAIL: Yes. 

ALEX BLUMBERG: And the reviews weren't ...

SAM ESMAIL: No. The reviews were not great. I was not getting any calls after that movie got released. And I was -- I was very concerned. And so this was kind of like, "Okay, here's my second at-bat." And if this was another swing, I didn't know if I was going to get a third at-bat. I mean, how many, you know, how many chances do you get?

ALEX BLUMBERG: Right. 

SAM ESMAIL: Right. 

ALEX BLUMBERG: When did you know that you -- when did you know you had a hit?

SAM ESMAIL: I mean, is it? I mean, you know -- I mean, you never… I mean, look -- I do think when we were in the middle of shooting season one and the reviews started kind of pouring in, and they were pretty unanimously good. And I was like, "Oh my god. Okay, this is -- this is a good" -- like I was letting it in. And we were filming a scene with -- with Rami who plays Elliot in Mr. Robot and -- and Frankie who plays Shayla out on the stoop. And in the middle of the shot, a cab rolls in with the ad for Mr. Robot on there. And we have to cut. And I remember thinking, "Okay, this is like -- okay, we're a real show -- like it's really happening." It ruined the shot but I got to say, it was like -- it was one of those surreal moments where I was like, it feels like -- it just started to feel like people were talking about the show in the city. 

ALEX BLUMBERG: Uh-huh.

SAM ESMAIL: And I remember thinking, "This is really cool." Like, people started stopping Rami, and -- and, you know, and it started to get crazy. And I just felt like there was just something in the air that summer, the 2015 summer when Mr. Robot was airing and we were shooting. It was just -- it just -- yeah, it was like -- it was pretty cool. 

ALEX BLUMBERG: Yeah.

SAM ESMAIL: It was like, "Okay, I can breathe easy. The show's going to be okay." 

ALEX BLUMBERG: Right. So is your life anxiety-free now? 

SAM ESMAIL: No. No, no, no, no. But the anxiety is a good type of anxiety. It's not worrying about car insurance, it's worrying about well, what's going to be a great, you know, episode of television, or what's going to be a great feature. You know, that -- that's the kind of anxiety I'm okay with. 

ALEX BLUMBERG: Is there still anxiety -- is there still that sort of existential anxiety, like ... 

SAM ESMAIL: Oh, that you could fail?

ALEX BLUMBERG: Yeah. 

SAM ESMAIL: Yeah, for sure. But you can't be anxious about it, you know what I mean? Like you just -- see at the end of the day, the one thing I kind of always go back to whenever I start writing something or think about filming something is, I have to be a fan of this. It goes back to that five-year-old kid when I saw French Connection. I want to enjoy this. It has to be enjoyable for me. And if that doesn't work, then -- then -- then it wasn't -- you know, then that's out of my control. Then that's not something I can, you know, sort of negotiate or -- or manipulate. Like, I -- it just -- it just -- if I can stay true to that, and if I end up enjoying it -- and by the way, that's how I felt about Comet. It did not end up working out -- outside -- outside of the audience of one, which is me. But I have to be okay with that, and I just have to weather that.

ALEX BLUMBERG: Uh-huh. Yeah. Yeah. So what about your parents. Like they didn’t want you to be a filmmaker. How do they feel about it now? Are they finally on board with you being a filmmaker?

SAM ESMAIL: No. My mom still talks about my cousins who, you know, they're -- they're lovely people. One's a doctor and married with three kids. And I think one -- I think they're about to have a grandkid. Another one's a lawyer. 

ALEX BLUMBERG: Yeah. 

SAM ESMAIL: And my brother is a lawyer for Twitter, actually. And -- and he just had his kid. And she -- that to her is success. 

ALEX BLUMBERG: She's like, "Why can't you be more like your brother?" 

SAM ESMAIL: Why can't you be like that. This is weird. 

ALEX: And you’re -- mom, Golden Globe!

SAM: Doesn’t matter… 


That wraps up my conversation with Sam Esmail.


Without Fail is hosted by me and produced by Molly Messick and Sarah Platt. It is edited by me and Devon Taylor. Peter Leonard mixed this episode. Music by Bobby Lord.


If you like Without Fail, leave us a review! Tell your friends about it. 


Thanks for listening.